5-modified pyrimidines from palladium catalyzed carbon-carbon coupling

Abstract

This invention discloses a method for the preparation of pyrimidine nucleosides modified at the 5-position of the pyrimidine ring using a palladium catalyst of the formula PdL3, wherein L is a ligand of palladium. Included in the invention are pyrimidine nucleosides modified at the 5-position prepared according to the method of the invention.

I claim: 
     
       1. A pyrimidine nucleoside modified at the 5-position of the pyrimidine ring prepared according to a method comprising the steps of: a) preparing a solution of a palladium catalyst of the formula PdL 3 , wherein L is triphenylphosphine (PPh 3 );   b) reacting a pyrimidine starting material containing a halogen leaving group attached to the 5-position of said pyrimidine starting material with a tetraalkyl tin compound of the formula R'SnR" 3 , wherein R' is a C1 to C4 alkyl, and R" is selected from the group consisting of a C1 to C7 carbonyl, a C1 to C5 carbalkoxy, a C1 to C3 alkenyl, a C1 to C4 alkoxy or phenyl (C 6  H 5 ), in the presence of the PdL 3  catalyst; and   c) isolating and purifying said pyrimidine nucleoside.   
     
     
       2. A compound of the formula ##STR13## wherein R 1 , R 2  and R 3  are independently H, alkyl, alkenyl, alkynyl, alkoxy, phenyl or halo and Y is ribose or deoxyribose. 
     
     
       3. A compound of the formula: ##STR14## wherein R 1 , R 2 , R 3 , R 4  and R 5  are independently halo, H, alkyl, alkynyl, alkoxyl, phenyl or cyano and Y is ribose or deoxyribose.